p-NJTKANlLINK PKKI'ARATION 5(1. p-Nitr aniline. P>endcr and Erdmnnn, Chcwischc Priiparatcnfawde, vol. ii. ]). 438. 25 grms. ace t anil ide. 25 c.c. acetic acid (glacial). 50 „ cone, sulphuric acid. 10 „ fuming nitric acid (sp. gr, 1-5). The acetanilide, acetic acid, and sulphuric acid arc mixed by means of a mechanica.1 stirrer and cooled in a free/ing mixture. The fuming nitric acid is then gradually added from a tap- funnel at such a. speed that, the temperature does not exceed 20 . After the acid has been added, the mixture is stirred for an hour and poured on to ice. The product is then diluted with water, left to stand for a time, filtered, washed, and dried on a porous plate. It maybe recrystallised from dilute alcohol, but is usually pure enough for further treatment. Yield is So per cent, of the theory ; the remaining 20 per cent, is ortho- compound and "remains in solution ; m. p. 207°. C(; H ,, N II . CO C II, + 1 1 N C), - N ( )., C(i 1 1 .,. N 1 1 . C O C I-T « + H,,O ' °i " The /'-nitracetanilide is either boiled with 2\ times its weight of concentrated hydrochloric acid, or heated on the water-bath with twice its weight of equal volumes of sulphuric acid and water until the liquid remains clear on diluting with water. The /MI it ran 5 line which is now present in the liquid as the hydro- chloride or sulphate, is diluted with water and precipitated by the addition of an excess of caustic soda or ammonia. When cold, the yellow crystalline precipitate is filtered, washed and re-crystallised from boiling writer. Yield, 25 grams. Ncx.c^iii.Nircocn, -i- 11,0 i no ^ N()O.C:(!II.,.NII,.IICI 1 ' H rii,('O(.>n Properties.— -Yellow needles; in. p. 147 ; soluble in hot water ; very soluble in alcohol.